Abstract2‐N‐Sulfonylaminoaryl disulfides can be converted into the corresponding benzo[b][1,4]thiazines in one pot when reacted with an electron‐rich alkene in the presence of a base and a substoichiometric amount of a copper salt. Depending upon the reaction conditions, and in particular the copper salt used, we observed the concurrent formation of variable amounts of the corresponding benzo[b][1,4]thiazine S‐oxides that are not the result of a post‐oxidation reaction. The overall procedure can provide simple access to benzo[b]thiazines or thiazine S,S‐dioxides by sequential reduction or oxidation of the crude reaction mixtures.
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